The End of the Year Is for Renegotiation

As the year winds down, a familiar impulse takes over.

New goals. New habits. New resolutions. The calendar turns, and it feels like a natural reset — a clean line between what was and what could be.

But January 1st doesn’t reset anything that matters.

The context you’re operating in doesn’t suddenly shift. The constraints don’t disappear. The tradeoffs don’t become simpler. You don’t wake up in a different reality just because the date has shifted

“What the end of the year actually offers is not a reset. It offers a checkpoint.

And checkpoints aren’t about adding something new. They’re about deciding what continues.”

Years ago, I wrote an essay called 12 Essential Principles for a Long and Happy Marriage. The final principle was the least romantic and the hardest one: be willing to renegotiate the contract. 

Not because something had broken, but because circumstances change. 

What two people need from each other at one stage of life isn’t guaranteed to hold forever.

That logic applies just as much to the relationship you have with yourself and with your employer.

Every organization, and every individual, makes an implicit contract when they start something. How success will be measured. What matters. What effort is worth sustaining. What the goal actually is.

The problem isn’t that these contracts are poorly designed. 

It’s that they are rarely renegotiated.

As conditions change, people keep operating under the same definition of success. The same assumptions. The same commitments. The same habits. Not because they’re still right, but because they were never examined again. 

That’s why the end of the year matters.

Not as a moment for resolutions.

But as a moment for renegotiations. 

When assumptions outlive their context

Every decision starts with a definition of success. Some of it is explicit. Some of it is implicit.

The explicit part is usually easy to name. The implicit part is harder, and often more consequential. It’s also the part most likely to go unexamined.

Looking again at what success looks like “now”, tends to surface assumptions that once made sense and no longer do. 

The assumptions quietly shape how time is spent, where attention goes, and which tradeoffs feel acceptable.

The challenge is that definitions of success don’t announce when they expire. 

Execution can remain solid even as the outcomes quietly stop making sense.

At that point, what needs attention isn’t effort or discipline. It’s relevance.

When discipline keeps reinforcing outdated measures of success

We tend to celebrate discipline without asking where it’s being applied. 

Staying the course. 

Following through. 

Not changing direction too quickly. 

All of that matters.

But discipline has a limit. When consistency outlives context, it stops being helpful.

Discipline is what happens when a definition of success gets reinforced over time. That only works if success is still being defined in a way that makes sense.

Sometimes what looks like focus is inertia. 

Sometimes what looks like commitment is loyalty to an agreement that no longer reflects current conditions. The direction itself isn’t wrong—it’s just no longer current.

And the hardest thing to question isn’t a goal. It’s the discipline that’s been built around it.

When commitments quietly turn into obligations

Some commitments are explicit. They live on calendars and roadmaps.

Others are less obvious.

They’re  roles you stepped into because something needed doing. Identities that once served you well. 

Responsibilities that solved a real problem at the time.

No one is enforcing these commitments now. No one is asking you to keep them. And yet they persist.

They don’t show up as tasks so much as carryovers —decisions that were never fully closed and continue to occupy space.

Much of what people experience as overload isn’t caused by too much work. It comes from things that were never meant to last this long.

I’ve seen this in my own career

Early in my career, I spent years in IT support roles. There was a time when I literally had a pager on my hip. Immediate availability wasn’t optional - it was the job. That discipline mattered. It was appropriate. It served me well.

The role changed long ago, but the behavior stuck. 

For years afterward, I still felt a pull to respond instantly, to treat interruptions as urgent even when they weren’t. In reality, very little of my work required that kind of immediacy.

There were rarely true emergencies.
But I was still operating as if there were.

That carried a cost. Not in time, exactly, but in cognitive load. Letting go of that discipline required a conscious renegotiation — acknowledging that what once mattered no longer needed to.

That’s why the end of the year matters.

Not because it demands change.

Not because it tells you whether the year was good or bad. 

It matters because it creates a checkpoint—a moment where continuation becomes visible.

A moment to see:

• Which assumptions are still being treated as current.

• Which commitments are still being honored by default.

• Which habits and efforts are still organized around an idea of success that may no longer apply.

Not everything needs to be revised.
Not everything needs to be replaced.
Not everything needs to be let go.

But some things deserve to be consciously renewed—or consciously released.

Berkson’s Bits…

Sometimes the most valuable thing you can say is "I don't know."

Even better, follow that up with a question like "what do you think?" or "what are we missing to help us understand this better?"

What I'm Reading...

As a companion to this week's newsletter, I am recommending "Quit" by Annie Duke. I have written about "kill criteria" and Annie Duke was a big inspiration for how I think about it.

Also, please share a recommendation for what you're reading/watching/listening to. I respond to every email.

When I wrote 12 Essential Principles for a Long and Happy Marriage, the final principle was "Be willing to renegotiate the contract." It wasn’t about fixing problems. It was about maintenance.

The work at the end of the year isn’t to stack new resolutions on top of old assumptions.

It’s to revisit what you originally agreed to optimize for. 

How you said you’d measure success. 

What you committed to do in service of that definition.

The contract you’re living under today may have been the right one once. The question is whether it still is.

That’s the real opportunity at the end of the year—not to start over, but to renegotiate with intention.

And often, the most important contract to revisit isn’t with a role, a company, or a plan.

It’s the one you made with yourself.

Wishing you a thoughtful close to the year—and a deliberate start to the next.

Looking forward to continuing the conversation...

Alan